


Undercover Under the Covers

by Wolves_of_Innistrad



Series: Jockstrap Collection [4]
Category: Teen Wolf (TV)
Genre: Alternate Universe - Human, BDSM, Bottom Derek Hale, Bottom Derek Hale/Top Stiles Stilinski, Collars, Dildos, Dom Stiles Stilinski, Enemies to Lovers, Fake/Pretend Relationship, Jock Straps, Leather, Leather Kink, M/M, Sub Derek Hale, Top Stiles Stilinski, Undercover, Undercover Cop Derek Hale, Undercover Cop Stiles Stilinski, Undercover as a Couple
Language: English
Status: In-Progress
Published: 2018-09-25
Updated: 2018-09-25
Packaged: 2019-07-17 09:41:01
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,277
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16093031
Author URL: https://archiveofourown.org/users/Wolves_of_Innistrad/pseuds/Wolves_of_Innistrad
Summary: When Derek and Stiles get assigned to work on the same undercover case Derek figures he can deal with Stiles' constant flirting and general off-putting childish behavior, until he finds out what the case involves.  Now he's forced to pretend to be not only Stiles' boyfriend, but his submissive, which wouldn't be that hard if he wasn't secretly a submissive already and finds that side he keeps hidden being thrust into the open has some very interesting side effects on his personality, his relationships and whether he's really as disinterested in Stiles as he's always told himself.





	1. The briefing

          When Derek walks into the meeting he almost balks at seeing Stilinski here. Or should he say Agent Stiles as he prefers. It’s not like anyone couldn’t learn to pronounce his name, in fact Derek had only taken what he felt was an acceptable half hour of practice before he could replicate the weird sounding moniker. Still, the new recruit preferred it and since his father was the Director, most people simply followed along with it.

It wasn’t so much that Derek disliked Stiles, sure he was brash and over affectionate at times, seemingly disrespectful to superiors, albeit most of the times that happened Derek did have to admit that Stiles was in the right and the higher ups were being facetious. Nevertheless something always rubbed him the wrong way when it came to Stiles, maybe he was just too young, too hyperactive, or even that he was the Director’s son and thus got away with more than someone like Derek who always had the deputy Director, Argent, on his ass.

Then again, it might have been the fact he let Argent _into_ his ass years ago that made their particular interactions so awkward and stiff, but that was something no one thankfully knew except the two of them and he planned on keeping it that way. Especially since Argent’s sister had been arrested for being a stalker, arsonist and attempted murderer, he didn’t need any trouble with that family.

Of course now here he was taking a seat next to Stiles, the other giving him that lackadaisical smile and what was clearly an inappropriate once over before turning back to their Intelligence officer, Agent Martin.

Now Agent Martin was at the small podium, fiddling with something on her computer, likely adding some last minute information she’d just received from one of her sources. It was kind of scary how much the woman could find about anyone, like she had little voices whispering where to go, who to talk to. It was uncanny, but it made their jobs a heck of a lot easier and as long as she was focused on the criminals it meant she wasn’t intruding on their lives. Derek had enough problems with that thanks to his nosy family and his pushy, resilient and downright abrasive friends.

“Now that you’re both here I have some news,” Agent Martin, Lydia, said with a flip of her strawberry blonde hair. He only knew that was the particular shade because Stiles had mentioned it repeatedly to one of the lab techs, Scott he thinks, when Derek had been eating lunch near them one day.

Clicking on something she brought up some files on the screen, Derek recognized the names, albeit vaguely. “This,” she used the cursor to circle around the photo of the man in question, “ is Deucalion, He’s got his hands in a little bit of everything, money laundering, smuggling, prostitution, racketeering. You name it he’s probably tried it at least once, and also never left any shred of evidence enough for us to truly nail the bastard.”

Shrugging, she continued. “Now recently we’ve discovered one of Deucalion’s biggest vices, an easy task to complete, but not so easy to follow up on. Our previous attempts have been fruitless, with multiple agents failing to get close enough to truly make any headway with Deucalion, or even any of his inner circle. No matter how charming, attractive or persistent they are, no one ever has seemed to catch Deucalion’s eye, and frankly it seems that’s the only way to get an in with him. His tastes seem to run along two very specific parameters, and that’s why we’ve called the both of you here.”

Derek looks sideways at Stiles, feeling as if he’s missed something,, which often is the case with Lydia. She has so many things running through her head she often expects everyone else to just keep pace and make the connections themselves.

Stiles though, it seems, is following her rapid pace, face screwed up in concentration as he stares at the photo and the info provided. “So what exactly are we supposed to do? Seduce him? Or just be attractive and his type?” Stiles asks, more serious now. It’s a trait Derek hasn’t had time to fully analyze but seemed true, that the sophomoric demeanor Stiles treats almost everything with tends to fall away, at least temporarily, while he’s truly focused on his task.

Lydia nods, clicking through to another slide filled with photos of different men, with a clear delineation down the middle showing two distinct “looks.” Clearing her throat, Lydia begins again. “As you’ll see on the left, Deucalion’s tastes run in two primary ‘types,’ namely lanky, doe-eyed young men with long legs, longer fingers and from what we can tell, motormouths.” There’s definitely a distinct hint of mirth in Lydia’s voice, like she’s enjoying this way too much as she stares at Stiles.

For his part Stiles leans back in his chair, chuckling to himself before throwing up his hands. “Alright, so that explains me then. I’m definitely his type, although I prefer my daddies a bit younger,” Stiles quips, licking his lips and casting a brief, furtive glance in Derek’s direction.

“Yes, you certainly fit the bill to a tee. The last bit is that, as you’ll see in the packets I’ll be handing you shortly, Deucalion has quite a taste for the leather community, with a bent towards BDSM as well. From our intelligence gathering it seems that he prefers this type of man, which Stiles best embodies, to act as a Dominant in his relations. Now considering how Domineering Stiles can be I’m sure that will be no problem for you, however,” Lydia then turns to Derek, “I believe Derek here might have some qualms about his role to play.

For all this time Derek has remained silent, passively absorbing all the information as always. Some like to say he broods, but he doesn’t see it that way, he just views wasted words as pointless. “Oh? And what will I be doing then?” Derek asks.  Frankly the fact that Lydia has even voiced a concern has put him on edge, he’s done undercover work before, he’s infiltrated gangs, mobsters, he doesn’t know how attracting the attention of some old man is going to be so different.

“Well,” Lydia says moving over to the other side of photos, “Deucalion appears to have a secondary type that he prefers. These men tend to be tall, bearded, somewhat surly, athletic and, most important to Deucalion, totally submissive… And I do mean that in the exact way you are thinking.”

There’s about five seconds where Derek just processes what she says before nodding his assent. It’s not something he'd ever admit to anyone, but he’s secretly always had a very, very submissive bent in bed. Only Argent and maybe one or two other men he’s been with have known. He hopes Argent isn’t the one that suggested him for that reason, but looking at the photos it seems he was picked more for his physical attributes than any sexual ones.

“So I’ll need to what? Submit to Deucalion, let him… Fuck me?” Derek asks, not sugar coating the words now that the topic has gotten this intimate already.

“We don’t know. It’s entirely possible that will never come to pass, however it may. The reason we’re sending you in as a pair is to help lessen that at the outset. If Deucalion believes the two of you are a couple then he might be less inclined to try something as quickly, but still be enticed enough at the prospect to let the two of you into his circle.”  Lydia finishes speaking but no one says anything, Derek is disturbed to find that the idea of being a pretend couple with Stiles repels him more than the thought of having to bend over for Deucalion. Then again, the though of having to be submissive to Stiles may be even worse than pretend dating, if that’s what she means.

A snicker breaks Derek’s concentration and he turns to Stiles, whose grin is wider than he’s ever seen it. “You want Derek to pretend to be my submissive boyfriend? Is that seriously what our roles are?” Stiles asks, incredulous. When Lydia nods he nearly snorts with his own laughter, eyes turning back towards Derek. “Oh, this I’d love to see. Mr. Alpha over here wouldn’t take an order from me if it was to duck and cover to avoid a bullet aimed at his head,” Stiles remarks, eyes brushing between Lydia and Derek, although they return to Derek more often than not.

“It’s a job. I’ll do whatever I have to in order to serve justice, even if it’s entirely inimical to my own desires,” Derek says flatly, and it’s true. He may like being submissive in bed, but he certainly doesn’t want to do it in front of other people, least of all Stiles. He’s not sure how he’ll do it, but that doesn’t mean he won’t try his best.

Stiles rolls his eyes, rearranging his long limbs in his chair again, always a bit akimbo. “Alright, if Derek’s game I am. Tell us everything we need to know Lyds,” Stiles says, receiving a look of warning from Lydia at the nickname.

They finish the rest of the briefing with little more interaction, both paying more attention to Lydia’s accounts of how the last agents failed, what pitfalls to avoid and what people they’ll be likely to encounter. By the time they’re through Derek has learned more about Deucalion and his inner circle than he probably knows about half his coworkers, and he feels confident that this mission will be a success.

That confidence drains away the next time he meets them both down at Jackson’s warehouse and sees what he's supposed to be wearing during the first outing.


	2. De-Briefing

**Summary for the Chapter:**

> This is just gratuitous description porn of clothing, bare with me and my Ibsen-esque writing

          “No,” Derek says, voice as brusque and flat as he can manage it. The outfit is, well, frankly the outfit is a wet dream come true for Derek, but the idea of having to wear it in public, to a leather club no less, puts him on edge. “I’m not wearing that.”

Jackson just smirks, looking towards Lydia with an “I told you so” grin.

“Derek, I know the outfit is… Revealing, but all our research points to this being exactly what will interest Deucalion the most. It’s not like Stiles isn’t going to be showing some skin too,” Lydia says, voice stern, but understanding enough.

“Stiles has pants,” Derek deadpans as he stares almost longingly at the outfit Jackson has laid out for Stiles.

Stiles, uncharacteristically, hasn’t said a word. Although his eyes have been almost glued to Derek’s outfit so Derek imagines he’s sublimating his normal flurry of words for a flurry of thoughts instead, and almost assuredly all filthy. It not like Stiles is actually unattractive. In fact, Derek thinks that if it weren’t for his personality Stiles would probably be exactly his type of man physically; roughly the same height, similar builds, a bit younger but not too young, probably more toned instead of overly muscular like most of the meatheads Derek gets hit on by.

“I’m sorry I think my brain broke for a minute, Jackson is really expecting Derek to wear this?” Stiles says, pointing towards the outfit. “You realize who you are designing this for right Jackson?”

Jackson scoffs walking over in front of Stiles and holding up a binder full of photos, swatches and reports. “This,” he says, slamming it down in front of Stiles, “is months of research and hours and hours of work I’ve done to perfectly tailor these outfits to _this_ man’s specific tastes, while avoiding any overlap with things we’ve had agents wear before, things we have noticed him find ugly or unattractive before, as well as having to hand design some of them and make sure they fit your measurements. So much of this mission rides on the physical appearance getting you noticed, we’ve learned from our mistakes. Some shit you bought at the local sex shop or off Amazon isn’t going to cut it. This is real, handcrafted leather. I made these all by hand or personally tailored them to fit your measurements, which God help me if either of you gained even one pound since your last measurement I will end you both.  So you'll both shut up, especially you Stilinski since having me dressing you will be the first time you haven't looked like a mess."

Derek feels cowed and he wasn’t even the one getting his ass handed to him, so he’s not sure how Stiles deals with it. Then again he’s not sure Stiles truly cares what anyone says to him, but at least Stiles seems to back down from joking.

“I’ll wear it,” Derek hears himself say, almost as if someone else is speaking through him. “It’s for the mission. Jackson and Lydia know better than me what Deucalion will like. If this is what it takes I’ll do it.”

That puts a smile on Jackson’s face and he nods towards a folding screen nearby. “Go try it on then. We need to make sure it fits and, more importantly, that it actually looks good. I only have your measurements so I don’t know what your body will look like in it,” Jackson says.

Immediately regret hits Derek. He knew he was going to have to wear this in the field, but he was hoping he could try it on in private, not doing so in front of the whole team here. Then again, he supposes it’s good practice for later, and Stiles is going to see it regardless so he takes a deep breath, grabs the articles of clothing and trudges towards the screen.

Wasting no time, Derek strips out of his own clothes, the rather drab but fitted suit he wore to the office. The cool air of the warehouse chills him as he grabs the first item of clothing. He pulls the jockstrap up past his hairy legs and muscular thighs, taking a bit of rearranging but managing to fit all of his ample endowment, both in the front and the back, into the leather jockstrap.

There’s an electric blue streak painted on the front, the jock sitting low on his hips despite the classic thick waistband all around. Derek can feel the straps perfectly lifting each ass cheek up, knowing that the hairy globes are on full display. If this were another situation and this was something he bought himself to wear he’d probably be hard as a rock just feeling the leather on him, how well it contoured to his body, but knowing he’s about to show off well… Actually, he’s still hard, and that might be a problem, but he has the rest of the outfit to put on still so he hopes his traitorous erection fades by then.

Next comes a pair of thick leather boots, then a leather harness. It only goes over one shoulder, and the metal of the O-rings are cold against his skin, but the leather itself is so soft and supple he almost forgets its there once he has it on. The biker jacket he slides on next, and he’s not sure how Jackson has tailored it so perfectly. It feels painted on, he knows for sure it wouldn’t close if he tried; then again that’s the point, he’s supposed to be exposed, but he still has a good range of movement despite how fitted it is. It also doesn’t take long to realize that it’s been tailored so not even an inch of the jacket covers up his ass in the back.

Now it’s down to just the last accessories, he avoids one of them to go for the jewelry, which is a fake clip-on nipple ring. He huffs a laugh at that, sliding the thing through his actual nipple piercing, knowing Jackson will have to get a real one for the final look now that he’ll know about it. He slips on the finger-less leather gloves, noticing the knuckles are cut out and chuckling. Then he’s left with just one accessory, the one he’d dreaded the most, even above the jockstrap.

It’s a leather collar. The inside is soft, some material he isn’t quite sure of padding it with the smooth leather on the outside. It’s all blue leather, like the stripe on the jockstrap, with a D-Ring in front. Once it’s on it’s tight enough he knows it’s there, but not tight enough to hurt or restrict his breathing, and once again he’s a bit scared at Jackson’s accuracy. Derek wishes he had a mirror to see how it all looks, but considering he’s still a bit chubbed up from the smell and feel of the leather he figures that’s something he can do later at home.

Deciding it’s now or never Derek steps out from behind the divider and immediately notices two things. First, Stiles’ jaw seems to unhinge as it drops so low, before he himself falls face first towards the asphalt as the chair he was leaning against goes off balance. The second is the self-aggrandizing and frankly conspiratorial look Jackson and Lydia share. Those two combined seem to imply that he looks exactly as he’s supposed to which does boost his confidence, even if he's pretty sure the shade of pink his ears are turning doesn't match his outfit.

Stiles is still recovering as he drags himself up off the floor, still gawking at Derek. Derek actually smirks at that, because as much as he knows Stiles has undressed him with his eyes, the man clearly wasn’t ready to see him like this and it shows.

Jackson steps up and looks him over with a critical eye now, clearly zeroing in on the nipple ring and glancing to meet Derek’s eyes. “This is… Wow, I didn’t expect it to be this perfectly fitted,” Jackson says. “Turn around.”

Derek does so, grinning to himself when he hears Stiles audibly choke on his own spit at the sight. All this time he’s never done anything but ignore Stiles’ lascivious looks and pointed comments, but if he’d known he could get under his skin so easily he might have done something sooner. Feeling cheeky he flexes his ass, feeling the meaty muscle bounce a little before snapping back to place.

There’s a whispered “Oh God...” that he knows comes from Stiles and he reaches up to cover his own smile because as much as he doesn’t want to be in public looking like this, if it means he can mess with Stiles he can deal with it.

Jackson coughs and he turns back around, watching the man not so subtly moving his clipboard over his crotch. Stiles catches his eye next and the man is looking at him like he’s never truly seen him before, and he guesses he hasn’t. Really, hardly anyone has seen him like this, as scary as it is to think, seen him for what he is inside. Biting his lip, Derek wonders how he’s going to deal with living out a fantasy of his wearing all this and being submissive, but then having to do it with Stiles, who he just knows is going to take every opportunity to mess with him and probably try to get handsy too.

And under normal circumstances he’d be able to report that to HR, but here they almost are required to do it so it’s going to be a struggle. Derek doesn’t think it’ll get any harder than this until Jackson waives Stiles off to try on his outfit. Frankly Derek hadn’t paid much attention to Stiles’ wardrobe for the mission, only that it included pants, unlike his own, so when Stiles walks back out looking like every fantasy he’s ever had he’s a bit stricken.

Stiles is wearing leather riding boots that go further up than he’d expected they did, and they must have lifts in them or a heel because he can already tell Stiles looks taller wearing them. He has leather pants too, the kind that look drawn on and there’s a noticeable bulge that makes Derek forget that he’s ogling Stiles and not the hottest leather daddy at Folsom.

Intellectually Derek had assumed Stiles was physically fit, but seeing the man with his chest bared, the hint of abs, more toned than muscular, those broad shoulders and well developed chest framed by the crossed harness he’s wearing. There’s small blue stripes going down each strap of Stiles’ collar and distantly Derek realizes with dawning horror that they match. That’s such a couple thing to do, but also a very Dominant one he feels, like Stiles, in their little game, is showing that Derek belongs to him even with their fashion choices.

For his part Stiles doesn’t have any jewelry, but he does have leather gloves, different than Derek’s and God help him he actually has the brief thought of how good it would feel for those long fingered leather gloves to be spanking his bared ass. There’s a leather policeman’s hat atop Stiles’ head along with some dark aviators that make him look like the kind of cop you’d see in a porno who was about to handcuff you and make you pay for your ticket the hard way.

Derek tries, he really does try not to let the way Stiles looks in the outfit affect him, but when Jackson has Stiles walk over by him and he has to actually tilt his head the slightest bit to meet Stiles eyes now that he’s actually shorter than the younger man he nearly whimpers. Thankfully the sound stays trapped in Derek’s chest, but he doesn’t miss the way Stiles smirks down at him as he brandishes the leather riding crop Jackson gave him because of course he did, wondering if Stiles realizes how affected Derek is.

Jackson asks them to do a few poses, more so for him to check the angles and make sure it all looks right. It’s during that time that Stiles says, in a deeper than usual, commanding tone that he’d never heard fall from the man’s lips “on your knees.”

Derek drops to his knees in a heartbeat, barely registering what he’s doing until it’s happened and he’s on his knees, legs spreads, hands on his thighs in prime position for a submissive. He actually has to catch his breath for a moment and pull himself back from whatever head space he was slipping into. He’d had dreams like this before, fantasies, watched porn. Heck, Argent had even indulged him in a very small way, but nothing had ever went this far. He’d never been dressed up like this, with someone he realized he was incredibly physically attracted to giving him orders while also dressed like he walked right out of a Tom of Finland drawing.

No one seemed to make a big deal out of Derek’s obedience at first, at least not until his eyes cast upwards and he watched a grin slowly spread on Stiles’ lips, could see his own reflection in the aviators looking like the perfect submissive and heard Stiles say “Good boy.”

There was a brief, horrible moment where a shiver actually went down Derek’s spine and he nearly preened at the words before he finally snapped himself out of it and stood up.

“Are we done here?” he asked, voice gruff and strained as he stared between Jackson and Lydia, dutifully ignoring Stiles.

“Yes, I think this is going to work perfectly. I mean you even have the body hair, which is a big plus for Deucalion,’ Lydia remarks, jotting something down in her phone before she walks off.

“I’ll make sure to get you a real ring for the nipple piercing,” Jackson says, but he has no other adjustments to make. “You can go though.”

Derek nods his assent and starts to march towards the door only to stop when he hears Stiles’ voice.

“Derek, don’t you think you’re forgetting something?” Stiles asks as Derek is halfway towards the warehouse doors.

With a roll of his eyes Derek turns, doing his best to look annoyed and not aroused at the sight of Stiles all dressed up like this. “What?”

Stiles laughs, pulling off the aviators to look at Derek clearly. “You’re going to wear that back to the office?” he asks, and as soon as he says it Derek looks down and nearly smacks himself.

Hurrying back behind the divider Derek undresses, then redresses in his normal attire. Well, almost. He leaves the jockstrap on because it feels too good against his skin and no one will know anyway. Putting the rest of his outfit in his bag he hefts it over his shoulder before walking back out, staring resolutely at Jackson only.

“Thanks. I’ll just hold onto these so they don’t get lost in one of these closets,” Derek says, not mentioning he also wants to try it on at home.

After that he walks out without another glance at Stiles or his infuriating smirk and his stupidly attractive everything. Save his personality, that still rankles Derek to no end.

And if when Derek gets home from work he puts his new outfit on and stares at himself in his full length mirror for far too long, touching himself, taking pictures and finally riding his favorite dildo in the full getup, no one needs to know. He still spends ten minutes washing the cum off of the leather, just in case.

**Author's Note:**

> I wanted to do something for the Anniverserary of Teen Wolf's finale but I was busy so this is late don't @ me! Anyway, I'm back on my Sterek bullshit again, with another Wip. Will I ever finish it? Who knows, find out next time on Wolfie can't fucking stop making Wips 20gayteen.
> 
> Provided I actually continue this we'll see some other people show up too besides Jackson and Lydia.
> 
> As always, a huge thanks to all my Wonderful Readers for all the comments, kudos and subs!


End file.
